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Taking your family to Hawaii is often thought of as a once-in-a-lifetime trip. If you’ve been following MileValue, you know that we strive to make those once-in-a-lifetime trips happen early and often. There are lots of ways to redeem your hard-earned miles to take your family on a long anticipated trip to Hawaii. 

Let’s look at some of the most efficient ways to spend those miles on a Hawaiian vacation. 

About Hawaii

Hawaii is a dream destination  for many, and what’s not to love? Pristine beaches, interesting culture, volcanic tours and all without the hassle of an international flight. Fortunately, there are lots of ways to get to Hawaii on points and miles. You just have to decide where you want to land. 

Hawaii is a series of islands, four of which are easily accessible for travelers. Moving between islands is possible, but time consuming. Hawaii-traveling veterans recommend that if you have less than a week, you should plan your trip for just one of the islands. But if you have more time, you may want to see two or even three, depending on the length of your trip. 

Before you decide how you’ll get to Hawaii, you need to decide which is the best island experience for you.

You also need to consider your starting point. Hawaii is a tolerable five- to six-hour flight from West Coast cities, such as Seattle or Los Angeles, and most routes to Hawaii will pass through these hubs.

If you are starting in the Midwest or East Coast, you may need to consider adding a positioning flight or a stopover to your itinerary to break up your travel or get you to the airport with the best pricing to Hawaii. 

Inter-Island Travel on Hawaiian Airlines

If your trip includes more than one island, you’ll need to arrange travel between them. Hawaiian Airlines is, not surprisingly, the dominant operator of inter-island flights. Round-trip flights from one island to another can cost as few as 15,000 miles. This is Hawaiian Airlines cheapest award level, so make sure you look at the cash prices. 

A search I ran for April showed cash flights for $119 and $79 between Kahului, Maui (OGG), and Honolulu (HNL) on two different days, but when priced with miles, the redemption rate was the same. It might be worth booking a $79 cash ticket instead of using miles.

How to Earn HawaiianMiles

You can earn HawaiianMiles by applying for the Hawaiian Airlines World Elite Mastercard or the Hawaiian Airlines Business Mastercard. Both come with substantial bonuses that’ll allow you to take a whole family to Hawaii.

The Platinum Card® from American Express

Earn 80,000 Membership Rewards® points after you spend $8,000 on purchases on your new Card in your first 6 months of Card Membership. Apply and select your preferred metal Card design: classic Platinum Card®, Platinum x Kehinde Wiley, or Platinum x Julie Mehretu.


American Express Membership Rewards points transfer to HawaiianMiles at a 1:1 ratio. You can earn these points by applying for any American Express card that earns Membership Rewards, such as The Platinum Card® from American Express or the American Express® Gold Card.

Southwest Airlines

How to Book Flights on Southwest

Southwest Airlines flies to Hawaii from select West Coast airports. Southwest uses dynamic, demand-based pricing for its flights and has a fixed value of about 1.4 cent per point for award flights. It’s worth a look to see if you can score an ultra-low deal. 

Availability for April 2022 shows one-way tickets between Los Angeles (LAX) and Honolulu for as few as 7,800 Rapid Reward points. Even if you’re traveling from the eastern half of the United States, it could be worth purchasing a positioning flight to the West Coast with a low-cost airline or by utilizing other points and miles to take such a cheap flight! 

The real power of the Southwest strategy is the use of the Companion Pass. Because the Companion Pass allows you to bring any friend onto a flight you are on for free, your cost per ticket is essentially cut in half. If you are starting from the West Coast, you could easily get yourself and a partner to and from Hawaii for 7,800 Rapid Rewards points per person while utilizing the Companion Pass.

Even without the Companion Pass, a 15,600-point round-trip flight to Hawaii from the West Coast is a great deal. Just remember to include the cost of any positioning flight when comparing options with other ways to get to Hawaii.  

How to Earn Rapid Rewards Points

You can earn Southwest points by applying for any of the Southwest-branded personal cards, such as the Southwest Rapid Rewards® Plus Credit Card, or business cards, such as the Southwest Rapid Rewards® Performance Business Credit Card. 

Chase Sapphire Preferred® Card

Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening.


Southwest is a transfer partner of Ultimate Rewards, so you can transfer points from Chase to Rapid Rewards at a rate of 1:1. 

United Airlines

Recently, United scrapped its region-based award chart in favor of a hard-to-predict dynamic pricing model. While this change caused some award tickets to become cheaper, most award prices became more expensive.

However, because United is a member of the Star Alliance, booking United flights through a partner helps you take advantage of another airline’s favorable award chart, while riding on United metal. 

How to Book United Flights Using Aeroplan

One of my favorite Star Alliance partners to use for booking United flights is Air Canada Aeroplan. 

The benefit of using Aeroplan points to book United flights is Aeroplan’s hybrid award chart based on both regions and distance. Aeroplan uses the distance of the flight within each region (or between regions) to determine the total cost of the award booking.

Aeroplan divides the world into four regions. Hawaii is included in the same travel region as the continental United States, which places flights to Hawaii into the North America region. 

One-way flights under 2,750 miles within North America cost 12,500 Aeroplan points. Because California is about 2,500 miles from Hawaii, San Francisco (SFO) or Los Angeles are among the few departure cities in the continental United States where you can snag this great pricing. 

However, all is not lost for those of us outside California. 

The distance-based chart tops out at 2,751 miles, which means that a flight from Phoenix (PHX) and a flight from New York (EWR) require the same number of points — 22,500 points per direction.

The maximum award price from anywhere in the United States to anywhere within the North America region is 22,500 Aeroplan points each way when booking award space on United. 

There are a couple drawbacks to using Aeroplan for United flights while flying to Hawaii. First, one of the powers of using Aeroplan is its stopover policy that allows you to book a stopover for just 5,000 miles. Unfortunately, U.S. cities aren’t eligible for the stopover program. 

Although it would be nice to take an evening off from flying while traveling from New York to Hawaii, Aeroplan’s stopover policy won’t help you here. 

Second, Aeroplan charges a partner booking fee of 39 Canadian dollars  (about $30 at the time of writing). While this fee is annoying, being able to find cheap award space to Hawaii can easily make this fee worth it.

Because utilizing Aeroplan will cost you CA$39 fee on top of taxes, make sure to double check United’s site to see if you can find a deal based on low-demand pricing. If you can, you may still be able to book a ticket for 22,500 miles, or even fewer, through and pay the required $5.60 in fees.

How to Earn Aeroplan Miles

You can earn Aeroplan miles with the new co-branded card with Chase, the Aeroplan® Credit Card. You’ll earn 3X points at grocery stores, on dining and on Air Canada purchases and 1X point on everything else.

Chase Sapphire Preferred® Card

Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening.


Aeroplan points have become increasingly easier to earn as they now transfer from American Express Membership Rewards, Chase Ultimate Rewards and Capital One Venture MIles.

How to Book United Flights with Miles&Smiles

Turkish Airlines and its Miles&Smiles program is another Star Alliance partner of United. Although the program recently devalued its points currency, they are still a great option for booking United flights. The drawback of using Turkish Airlines compared to Aeroplan is the difficulty of earning points and some technological stress. 

Direct flights from the mainland U.S. to Hawaii are better priced through Turkish Airlines than through Air Canada. According to the award chart, round-trip, direct flights go for 20,000 Miles&Smiles miles in economy, 30,000 miles in business class and 50,000 miles in first class. Flights with connections cost 5,000 more each way. 

Turkish Airlines has been making some headway when it comes to the ease of booking award space with partners. Previously, you weren’t able to book United award space online and were forced to call Turkish airlines reservations. Booking on the phone costs an additional $25 booking fee, so being able to book online is helpful.

However, the award space you find on United can’t always be found on Turkish Airlines website, even though it’s still bookable as award space. In this case, you still have to book via phone:

  • Search for award space using and write down the flight numbers of each leg of the flight you want to take. 
  • Call the Turkish Airlines reservation desk at 800-874-8875 and tell them the exact flights you want to take leg by leg. 
  • Once the agent has located the award space, ask them to put the ticket on hold for you while you transfer points to your Miles&Smiles account. 
  • Once the points are in your account, call the reservation desk back and ask them to book the award space. Turkish Airlines will hold award space for up to 72 hours. 

How to Earn Miles&Smiles Miles

Of the flexible point currencies, Citi ThankYou Points and Capital One Venture Miles transfer to the Miles&Smiles program. You can earn Citi ThankYou Points by applying for the Citi Premier® Card. The Capital One Venture X Rewards Credit Card and the Capital One Venture Credit Card can help you earn Capital One Venture Miles

Capital One Venture X Rewards Credit Card

Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel


American Express® Gold Card

Earn 60,000 Membership Rewards® points after you spend $6,000 on eligible purchases with your new Card within the first 6 months. Terms Apply.


As of this writing there are no Turkish Airlines-branded credit cards on the U.S. market. 

American Airlines

American Airlines adoption of the dynamic pricing model was a disappointment for many, but you can still find decent deals using American Airlines award space. These options are probably better suited for those of us located in the Midwest or the East Coast, as our West Coast friends have cheaper options to fly to Hawaii already. 

How to Book American Airlines to Hawaii

American Airlines dynamic pricing is an advantage when searching for off-peak or other low demand tickets. If your trip dates are flexible, you may be able to find a Web Special award, which is a discounted award ticket with a few restrictions on cancellation and seat selection. The discount for a Web Special ticket compared to a standard award ticket is generally 5,000 to 10,000 AAdvantage miles. 

A standard one-way award ticket to Honolulu starts at just 20,000 AAdvantage miles originating in New York (JFK), Chicago O’Hare (ORD) or Dallas (DFW). No matter where in the U.S. you’re located, you can get to Hawaii cheap. 

How to Earn AAdvantage Miles

You can earn American Airlines miles by applying for the AAdvantage® Aviator® Red World Elite Mastercard® or one of the many Citi-branded credit cards, such as the Citi® / AAdvantage® Executive World Elite Mastercard®

Although Citi temporarily allowed transfer of ThankYou Points to American Airlines, this program has ended, and no flexible points currently transfer to American Airlines.

However, American Airlines flights are bookable using British Airways Avios, which can be transferred from American Express Membership Rewards, Chase Ultimate Rewards or Capital One Venture Miles.

Alaska Airlines

How to Book Alaska Airlines flights to Hawaii

Alaska Airlines probably isn’t the name that comes to mind when you think of a beach island vacation. However, flying with Alaska is a great way to get to the warm beaches of Hawaii. 

Alaska Airlines operates several nonstop flights in both economy and business class out of multiple West Coast hubs, including Seattle (SEA); Portland, Oregon (PDX); and Los Angeles . Economy seats start at 15,000 miles while business class seats will run you an absurd 80,000 points each way.

How to Earn Alaska Miles

The problem with Alaska Airlines is the difficulty in getting points. Outside of the co-branded Alaska Airlines business and personal card with Bank of America, topping off your Mileage Plan account is difficult.

Alaska Airlines has no transfer partners with some of the better known flexible points. Marriott Bonvoy points convert to Alaska Airlines at a ratio of 3:1, which is generally not a good use of Marriott points.

How to Book Alaska Airlines using Avios

If you can’t get your hands on any Mileage Plan miles, there’s still a way to book an Alaska flight to Hawaii. 

Because Alaska Airlines is now a member of the Oneworld alliance, you can book Alaska flights with a variety of Oneworld partner currencies, including British Airways Avios. 

You can purchase award availability on an Alaska flight using your Avios starting at 13,000 Avios for economy. You can convert American Express Membership Rewards, Chase Ultimate Rewards or Capital One Venture Miles to British Airways Avios to book your Alaska Airlines tickets.

Keep in mind, Alaska operates its Hawaii-bound flights from the West Coast, so if you’re starting from somewhere else, you’ll have to book a positioning flight to get to a city that Alaska Airlines departs from. 

How to Earn Avios

There are a plethora of opportunities to earn Avios points as Aer Lingus, British Airways and Iberia all earn Avios, which are transferable between the programs. The Aer Lingus Visa Signature® card, the British Airways Visa Signature® card or the Iberia Visa Signature® Card each earn solid bonuses and you can get the bonus from each card.

American Express Membership Rewards Points, Chase Ultimate Rewards Points and Capital One Venture Miles all transfer to Avios partners. 

Final Thoughts

A trip to Hawaii is well within reach with these strategies. The two determining factors for which airline to use is your points availability and your departure city. West Coast folks should look to see if they can snag a discounted Southwest ticket or book one of many available flights on Alaska using either Mileage Plan miles or Avios. 

If you’re starting from somewhere other than the West, take advantage of the Aeroplan award chart or find a deal on American Airlines. If you don’t see the award availability, keep checking or try a different partner’s site within the same alliance. If you find the award you want, but it isn’t coming up on the partner’s site whose point currency you wish to use, call the airline to book the award ticket. 

Of course, if you don’t want to hassle with the research and stress of finding the perfect award ticket, you can always use our award booking service, and we’ll find the most efficient way to use your miles to get you on the sandy shores of the Aloha State.